Hometown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Hometown Vacation
An easy way to experience this city is with a customized Hometown vacation package. Base yourself in the neighborhood of The Loop, which is great for bars and pubs, history and festivals or go someplace else — our package deals are all about you. Eager to venture out and explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the most popular places to visit during your trip to Hometown. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Hometown today.
Top Hometown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Hometown?
Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $174 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,193 reviews)
"The room was clean for the most part , all else is well a bit worn out , paint peeling off in many areas,its an old building but given the price range per stay should kept in a much cleaner conditions ."
Reviewed on Aug 28, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $194
CA $231 total
Sep 21 - Sep 22
includes taxes & fees
8/10 Very good! (2,112 reviews)
"The main lobby of the hotel was very nice but the rooms and bathrooms needs some upgrades for the lobby to be so elegant. The staff was very nice and in a good area."
Reviewed on Aug 28, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (876 reviews)
"Clean rooms, great location"
Reviewed on Aug 28, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
What to do in Hometown
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Frequently asked questions
How much does a Hometown vacation package cost?
You'll find cheap prices from CA $1,361 on Expedia for your Hometown getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Hometown costs.
What are the cheapest months to go to Hometown?
You can generally find lower prices and better availability in January, February and November. Browse our cheap Hometown vacation packages and you could score some great off-season discounts.
How many days is enough for Hometown?
Hometown vacations can be as short or long as you like, but to really sink your teeth into this destination, we'd suggest 2 days is a good ballpark. With this timeframe, you can visit major attractions like Moraine Valley Community College Fine and Performing Arts Centre and Lake Katherine Nature Centre along with underrated gems. Don't forget to visit cool neighbourhoods such as Archer Heights and Clearing either. If you're clever with your time, you can even schedule a day trip from Hometown too.
How to find the best Hometown package deals?
Finding a cheap Hometown package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Hometown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Hometown vacation as a package?
You can enjoy significant savings on your Hometown retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Hometown?
If you have your Hometown travel dates confirmed, book early to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Hometown?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Hometown.
- Set your budget: Consider costs such as flights, meals and transportation when calculating how much to set aside for your trip to Hometown. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
- Decide how many days away: Start by making a list of all the attractions you want to experience in Hometown. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Hometown vacation package.
Explore a world of travel with Expedia
- All Inclusive Resorts and in Chicago
- Lincoln Park Hotels
- Pet-Friendly Hotels in Chicago
- Cheap Hotels in Chicago
- Cheap Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Motels in Oak Lawn
- Marriott Hotels & Resorts in Chicago
- River North Hotels
- B&B in Oak Lawn
- Hotels near O'Hare Intl.
- Hotels near McCormick Place
- Hotels near SeatGeek Stadium
- Motels in Chicago
- Hotels near Midway Intl.
- Hotels near United Center
- Hotels near Soldier Field
- Hotels near Wrigley Field
- Hotels near Advocate Christ Hospital and Medical Center
- Bridgeview Hotels
- Magnificent Mile Hotels
- Hotels near Navy Pier
- West Loop Hotels
- Hotels near Millennium Park
- Hotels with Free Airport Shuttle in Chicago
- Vacation Homes in Hometown
- Chicago Hotels
- Hotels with Free Parking in Chicago
- The Loop Hotels
- Flights from London (YXU) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from O'Hare Intl.
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Calgary (YYC) to Chicago (MDW)
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Flights from Victoria (YYJ) to Chicago (ORD)
- Flights from Windsor (YQG) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights to Bridgeview
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Philadelphia (PHL) to Chicago (MDW)
- Flights from Montreal (YUL) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Chicago
- Flights from Ottawa (YOW) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (MDW)
- Flights from Ottawa (YOW) to Chicago (MDW)
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from Midway Intl.
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights to Chicago
- Unity Temple
- Centennial Beach
- Garfield Park Conservatory
- Lincoln Park Zoo
- Chicago Riverwalk
- Visit The Loop
- Ann and Robert H. Lurie Children's Hospital
- Robie House
- The Loop Vacations
- Downtown Chicago Vacations
- Water Tower Place
- Lakeview Vacations
- Griffin Museum of Science and Industry
- Art Institute of Chicago
- Grant Park
- Frank Lloyd Wright Historic District
- Visit Chicago
- Navy Pier
- Ernest Hemingway Museum and House
- United Center
- Millennium Park
- Chicago Theatre
- Buckingham Fountain
- Montrose Beach
- Willis Tower
- 875 North Michigan Avenue
- International Museum of Surgical Science
- Chicago Vacations
- Phoenix Vacations
- Golf Vacations
- Marina City
- Visit Downtown Chicago
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
